Daymond John discovered that he was in charge of his own destiny at age 10, and he never looked back.

John recently sat down with Jay Shetty in a recent episode of On Purpose with Jay Shetty to share some of the highlights of his career and the biggest lessons he has learned in creating a brand and building a team. 

Today, the man known as the People’s Shark on the long-running hit show Shark Tank, is a master negotiator, innovative designer, and successful entrepreneur. 

Like Jay Shetty, John had a ground-level education in real life. The lessons they both learned proved invaluable to their future success in business and self-development.   

Starting Early

When his single mother needed help making ends meet, 10-year-old Daymon John took a job handing out flyers for $2.25 an hour. That experience shaped him in ways he couldn’t have imagined. 

According to John, taking charge of his destiny at the age of 10 was the catalyst for his success later in life. His job handing out flyers on the street helped make ends meet in his single-parent household and took some of the pressure off. 

With John’s help, his mother didn’t have to juggle the income from her three jobs to try to meet their needs and wants. John could buy new clothes or shoes without feeling guilty for asking for them. 

John admits that at the time he didn’t fully grasp all that he was gleaning from his young entrepreneurial ventures. As the years have passed, however, he has seen how it has served him well. Later in life, it was the boost he needed to take his self-taught education in taking responsibility and working hard out into the world and make a name for himself.   

Go Big, Not Cool

After working so hard to pay for his own clothes and shoes, Daymond John learned to appreciate fashion. In the beginning, he says he just wanted to make cool clothes for cool people, but he struggled to figure out how to get his designs noticed. 

John couldn’t afford to make enough clothes to send a piece to every big name in the business in the hopes they would notice and wear one of his pieces. Instead, he had to start with the people around him.  

First, he realized that his clothing needed to solve a problem for someone. He decided to focus on men who wore big and tall sized clothing. 

“The big guys didn't have options for clothing,” he explained to Jay Shetty. “They only had a white, Rochester big-and-tall white shirt, a black shirt or custom-made clothing.” 

Next, he had to try to get his clothing in front of the right people.

“So if I only had money for 50 shirts and gave the 50 shirts to all the cool kids, they wore it one time, and threw it away,” he told Jay Shetty. That felt like a waste of clothing to someone who had grown up appreciating every piece of clothing he owned. 

He needed to start elsewhere. As he looked around his neighborhoods, he found the perfect demographic right in his own backyard – bodyguards and bouncers at popular clubs. Whereas influencers and “cool kids” only saw clothing as throwaway items, the big and tall audience loved wearing his designs.

“The big guys wore it 10 times a month,” he told Jay Shetty. “And where are those big guys? They were always in front of the red rope. They were always in front of the club. They were the guys who were the bodyguards. I built influence with them first.”

As people began to notice his shirts on the bouncers, they began to ask questions. At first, he downplayed the “coolness factor” of the shirts, which drove the mystery and demand up even more. Eventually, big name people were interested in getting their hands on his clothes, and his business exploded. 

John believes knowing where and who to advertise to made all the difference in the world.

Window Shoppers Rule the Wallet

John’s time in the worlds of business and fashion were successful because he looked at marketing in new and different ways. This not only led him to bouncers, but also to window shoppers. 

“Window shoppers go into the store and go, ‘You know, one day when I get money, I'm gonna buy those Y-3s,’” Daymond John told Jay Shetty. When a window shopper saves up and is finally able to buy something they want, they tell everyone, becoming a free brand ambassador.

“They’re gonna tell a million people, ‘Man who looks like a good Y-3 baby?’, then they became your ambassador. That person just shared it with 1000 people,” he said.

John calls this type of expanding and authentic marketing, “power shift dynamics”. This type of marketing reaches a different spectrum of people – people who will authentically get the word out about products they love. Their influence is powerful, and John urged listeners not to lose sight of that.

“These people are extremely, extremely important,” he said to Jay Shetty. “That's where the power shift happens. Because what happens is you build an influence with people. They're influencers too. They are just talking about it in a different way.”.

90-Second Influence

Influence is a word that is thrown around often these days.  Having influence and building a brand is a vital part of business success.  For John, the initial impact of a first meeting carries the least weight. 

“How can you build influence in 90 seconds?” John asked listeners. For him, an elevator pitch doesn’t do the trick to make an impact or win his interest. 

“People are very transactional,” he explained to Jay Shetty. “They think right then is the negotiation. That's not the negotiation. The negotiation is when I leave that elevator and I pull your name up on Instagram. That's where my due diligence and influence has started. Because then all the things you said to me in the elevator, I either looked on your social media or pulled you up or looked at the company you work for.”  

With that information, he then has a choice. If he’s interested, he seeks further contact. On the reverse side, if he sees red flags in their social profiles, he will not pursue it. The deeper influence seen through social media profiles has more bearing on if John pursues anything or not.  

“What I didn't realize about negotiation is that negotiation doesn't start when you get to the table. It starts way before you get to the table,’ John told Jay Shetty. His new book, Powershift, includes instruction first on creating influence, then on negotiating the deal, and finally on the post-negotiation relationship. 

Daymond John’s Process For Mentorship

The world of entrepreneurial business can be a lonely one, especially for those who are self-taught or are navigating uncharted waters. Daymond John believes having a mentor plays a vital role in growth and development.  

While Jay Shetty and Daymond John both live by the practice that learning under someone is crucial to personal and professional success, they acknowledge that finding the right match takes work. John is in a unique position of being highly sought after to fill the mentor role for many aspiring young business people and designers.  

“What is the process to become a mentor?” asked Jay Shetty. “What does that look like when someone's asking you for mentoring?” 

Step 1:  Be Honest

First, John cautions people to be honest about why they are seeking a mentor. If it is just to have a successful person rub off on them, they need to check their motivations. He also challenged listeners to think of what is in it for the mentor. If they give and give and give but get nothing in return, there is no relationship there. That is not mentoring.  

Step 2:  Be Realistic

“That's the challenge that I find with a lot of the people who seek out mentors,” he explained to Jay Shetty. “Are the mentors accessible? You can try to get a hold of me as a mentor, and hopefully I could be one, but that's why I write the books and do social media. You're going to talk to me, well, one time every six months.” 

Instead, John encouraged listeners to seek out powerful local mentors who are more widely available.  

“If you have somebody that has a car dealership locally in your neighborhood, who's been there for 20 years, that person understands the fundamentals of business just like anybody else,” John told Jay Shetty. “They've been through inflation. They've been through changing of technology. They've been down to all kinds of stuff, right?”

Teamwork Makes the Dream Work

As the owner of several multi-national businesses, Jay Shetty has experienced how difficult it can be to find the right people to fill professional and support roles. He asked Daymond John how he manages to find the right people for his teams. 

“As a growing entrepreneur with multiple businesses that are growing for myself, and I speak to entrepreneurs in the same space all the time, we find recruitment is probably the hardest thing,” Jay Shetty admitted. “It's a genuine challenge.” 

Daymond John takes a different approach than most, hiring people he’d already worked with as interns or third-party vendors.

“I noticed that the interns came to the office before people who got paid, and they would leave after,” he told Jay Shetty. “They are the ones who I would end up hiring that year or five years down the road. They came into the office and they were problem solvers.”

To Daymond John, hiring someone is almost like dating – you’re looking for the right fit that you can put up with for a long time.  

“There are two questions I like to ask them,” he told Jay Shetty. “‘Do you look in the toilet after you get up from the toilet?’ If they say no, they're lying. I also ask, “What has ever happened to you that was out of your control after you were 15 or 16 years old?’”

He uses the latter questions to gauge two things – their level of responsibility in a time of crisis and the problem-solving skills they bring to the table. John looks for employees who can continually adapt and grow.  

Jay Shetty and Daymond John agree that unless someone is able to continue to see and conquer areas of growth, their work will plateau. John compares this ability to a Swiss Army Knife – good employees use and sharpen all the tools at their disposal so they can remain useful and relevant. 

Finding those people is what makes a team successful. 

Mistakes in Negotiating

Daymond John has spent most of his life learning and experiencing the ins and outs of the business world. One of the skills he’s worked hardest to hone is negotiation. He shared some of the biggest mistakes he sees when it comes to people bringing a deal to the table.  

Mistake #1: Blurry Boundaries 

Have boundaries set going into the negotiation. It’s important to know where you’ll be willing to settle and what your ultimate end goal for the deal is. 

Mistake #2: Not Listening

Humility and respect will go a long way at the negotiation table, and it shows in how well both parties listen to each other. Negotiations break down when one or both parties stop caring about the other person, fail to listen, and start interrupting. 

“You're supposed to communicate like your face is built, right?” John said to Jay Shetty. “Like you have one mouth and two ears, right? Listen twice as much as you could talk.” Listening helps ensure that information is received in its entirety. 

“When people are communicating with you, almost the most valuable piece of information you're trying to share is at the end,” John told Jay Shetty. “A lot of people try to cut people off and stuff like that and miss it.”

Mistake #3: Bad Body Language

Not shaking hands, not making eye contact, and not remembering the person’s name rank at the top of the list when it comes to body language that will kill a negotiation. Meeting people respectfully with your words and your body language at the negotiating table will reap rewards. 

Negotiate With Yourself & Know Your Why

Although he’s a master negotiator, John told Jay Shetty the one person who challenged him most at the negotiation table was himself. 

Several years ago, Daymond John had a cancer scare. After undergoing a series of tests, there was a two-week wait before the tests came back. Waiting was the hardest part. Two weeks is a long time to mull over how he would handle it if the results were positive.

John decided to logically weigh both sides:  give up or fight. John decided that living his life to the fullest was his strongest move. Giving up has never been in his nature. Thankfully, the results came back clear, and he strengthened his resolve to live life to the fullest.  

And at the end of the day, knowing his why and staying true to his focus has been the staying factor for John’s success. The life he has built has withstood the ever-changing climates of both business and fashion and respecting himself and others serves as the foundation.  

These days, John leans into the legacy he is creating for his family and the larger community.  He is proud to leave behind a personal brand that focuses on the dignity and respect for people across the board; not just those whose names are in lights.

More from Jay Shetty & Daymond John

Listen to the entire On Purpose with Jay Shetty podcast episode on “How to Transform Any Outcome and Achieve Any Outcome” now in the iTunes store or on Spotify. For more inspirational stories and messages like this, check out Jay’s website at